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Chemical Compound Review

AR-1L8646     (2R,3R,4S,5R,6R)-2- [(2S,3S,4S,5R)-3,4...

Synonyms: AC1L3M3Y, 470-55-3, 11036-79-6, 127230-14-2, 128301-28-0, ...
 
 
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Disease relevance of Stachyose

  • Cortical vesicles transiently undocked in the presence of tetanus toxin were subsequently fusion incompetent although to a large extent they retained their ability to redock when stachyose was diluted [1].
  • Furthermore, proteoliposome reconstitution assays showed conclusively that the channels formed by protein F, as well as by unfractionated outer membranes, allowed the diffusion of a tetrasaccharide, stachyose, at a significant rate, indicating that these channels are much larger than E. coli porin channels [2].
  • This analysis demonstrates that (1) raffinose content in leaves increases upon heat stress in wild-type but not in the GolS1 mutant plants; and (2) the level of raffinose is enhanced and stachyose is present at normal temperature in HSF3 TPs [3].
  • Soybean flour contains raffinose and stachyose considered to be responsible for flatulence often associated with these products (J.J. Rackis, D.H. Honig, D.J. Sessa, and F.R. Steggerda, 1970). alpha-Galactosidase, produced on wheat bran, hydrolyzes the galactooligosaccharides of soybean milk [4].
  • When Bacteroides ovatus is grown on guar gum, a galactomannan, it produces alpha-galactosidase I which is different from alpha-galactosidase II which it produces when grown on galactose, melibiose, raffinose, or stachyose [5].
 

High impact information on Stachyose

  • The oxygen affinity of hemoglobin varies linearly with the chemical potential of water in the bathing medium, as seen from the osmotic effect of several neutral solutes, namely sucrose, stachyose, and two polyethyleneglycols (molecular weights of 150 and 400) [6].
  • Stachyose (2.6 osmol/kg) appears to inhibit cortical granule exocytosis by eliciting formation of a granule-free zone (GFZ) in the egg cortex which pushes granules away from the plasma membrane thus preventing their fusion [7].
  • Lytechinus pictus and Strongylocentrotus purpuratus eggs were exposed to 0.8 M stachyose or 40% (wt/vol) dextran (average molecular mass of 10 kD) in artificial sea water, activated with 60 microM of the calcium ionophore A23187, and then either fixed with glutaraldehyde and embedded or quick-frozen and freeze-fractured [7].
  • Chain Elongation of raffinose in pea seeds. Isolation, characterization, and molecular cloning of mutifunctional enzyme catalyzing the synthesis of stachyose and verbascose [8].
  • The DLDH mutants lost their ability to oxidize or grow with galactose or melibiose as sole carbon source and showed reduced oxidation and growth on raffinose or stachyose [9].
 

Chemical compound and disease context of Stachyose

  • In order to test the hypothesis whether galactose released from raffinose and stachyose could be a source of absorbed galactose and a cause of elevated gal-1-P six patients with galactosemia (aged 6-24 years), underwent a raffinose- and stachyose-poor dietary regimen for 2 weeks [10].
  • Conjugating bovine trypsin with oligosaccharides maltotriose, raffinose and stachyose increased its thermostability and suppressed autolysis, without affecting its cleavage specificity [11].
 

Biological context of Stachyose

 

Anatomical context of Stachyose

  • At concentrations up to and including 0.6 M, stachyose was without effect on the A23187-induced acrosome reaction [12].
  • 1. The objective of this study was to evaluate whether the oligosaccharide stachyose enhances gastrointestinal tract health by fermentation and proliferation of desirable bacteria species and thus affects growth performance and nutrient digestibility in broilers [16].
  • These experiments demonstrated that feces could be made void of raffinose and stachyose, but chick growth performance was not significantly (P > 0.05) improved by enzyme treatment [17].
  • Carbohydrase supplementation decreased (P < 0.05) the concentration of stachyose in freeze-dried digesta from the proximal and distal small intestine [18].
  • Galactose released from raffinose and stachyose may be absorbed and contribute to elevated gal-1-P values in erythrocytes of galactosemic patients [10].
 

Associations of Stachyose with other chemical compounds

 

Gene context of Stachyose

  • Average daily gain and feed conversion ratio were influenced by alpha-Gal and stachyose supplementation [23].
  • A proteoliposome, containing the isolated porin conjugate, was prepared to measure permeability of the sugar stachyose [24].
  • The final preparation had a specific activity of 9.09 nkat stachyose formed per milligram of protein [25].
  • Trace quantities of lupanine were identified as the alkaloid in jackbean. alpha-Galactosides were present in all the legume seeds, stachyose being the predominant galactoside in lima beans, African yam bean and jackbean, and verbascose in pigeon pea [26].
  • 6-phosphate D-Gal and stachyose are 20 times weaker inhibitors than D-Gal for induced CRP mediated agglutination, in contrast, these sugars are only 6 times weaker for CRP(N) [27].
 

Analytical, diagnostic and therapeutic context of Stachyose

References

  1. Calcium-regulated exocytosis is required for cell membrane resealing. Bi, G.Q., Alderton, J.M., Steinhardt, R.A. J. Cell Biol. (1995) [Pubmed]
  2. Identification and characterization of porins in Pseudomonas aeruginosa. Nikaido, H., Nikaido, K., Harayama, S. J. Biol. Chem. (1991) [Pubmed]
  3. Galactinol synthase1. A novel heat shock factor target gene responsible for heat-induced synthesis of raffinose family oligosaccharides in Arabidopsis. Panikulangara, T.J., Eggers-Schumacher, G., Wunderlich, M., Stransky, H., Schöffl, F. Plant Physiol. (2004) [Pubmed]
  4. Alpha-galactosidase production and use in a hollow-fiber reactor. Smiley, K.L., Hensley, D.E., Gasdorf, H.J. Appl. Environ. Microbiol. (1976) [Pubmed]
  5. Purification and characterization of two alpha-galactosidases associated with catabolism of guar gum and other alpha-galactosides by Bacteroides ovatus. Gherardini, F., Babcock, M., Salyers, A.A. J. Bacteriol. (1985) [Pubmed]
  6. Protein solvation in allosteric regulation: a water effect on hemoglobin. Colombo, M.F., Rau, D.C., Parsegian, V.A. Science (1992) [Pubmed]
  7. High molecular weight polymers block cortical granule exocytosis in sea urchin eggs at the level of granule matrix disassembly. Chandler, D.E., Whitaker, M., Zimmerberg, J. J. Cell Biol. (1989) [Pubmed]
  8. Chain Elongation of raffinose in pea seeds. Isolation, characterization, and molecular cloning of mutifunctional enzyme catalyzing the synthesis of stachyose and verbascose. Peterbauer, T., Mucha, J., Mach, L., Richter, A. J. Biol. Chem. (2002) [Pubmed]
  9. Characterization of the dihydrolipoamide dehydrogenase from Streptococcus pneumoniae and its role in pneumococcal infection. Smith, A.W., Roche, H., Trombe, M.C., Briles, D.E., Håkansson, A. Mol. Microbiol. (2002) [Pubmed]
  10. Leguminosae in the diet: the raffinose-stachyose question. Wiesmann, U.N., Rosé-Beutler, B., Schlüchter, R. Eur. J. Pediatr. (1995) [Pubmed]
  11. Thermostable trypsin conjugates for high-throughput proteomics: synthesis and performance evaluation. Sebela, M., Stosová, T., Havlis, J., Wielsch, N., Thomas, H., Zdráhal, Z., Shevchenko, A. Proteomics (2006) [Pubmed]
  12. The effect of permeant and impermeant osmoticants on exocytosis in guinea pig sperm. Green, D.P. J. Cell. Sci. (1991) [Pubmed]
  13. Genetic analysis of seed-soluble oligosaccharides in relation to seed storability of Arabidopsis. Bentsink, L., Alonso-Blanco, C., Vreugdenhil, D., Tesnier, K., Groot, S.P., Koornneef, M. Plant Physiol. (2000) [Pubmed]
  14. Identification of peptide mimetics of xenoreactive alpha-Gal antigenic epitope by phage display. Lang, J., Zhan, J., Xu, L., Yan, Z. Biochem. Biophys. Res. Commun. (2006) [Pubmed]
  15. Investigation into the ability of roots of the poikilohydric plant Craterostigma plantagineum to survive dehydration stress. Norwood, M., Toldi, O., Richter, A., Scott, P. J. Exp. Bot. (2003) [Pubmed]
  16. Effect of stachyose supplementation on growth performance, nutrient digestibility and caecal fermentation characteristics in broilers. Jiang, H.Q., Gong, L.M., Ma, Y.X., He, Y.H., Li, D.F., Zhai, H.X. Br. Poult. Sci. (2006) [Pubmed]
  17. The effect of enzyme treatment of soybean meal on oligosaccharide disappearance and chick growth performance. Graham, K.K., Kerley, M.S., Firman, J.D., Allee, G.L. Poult. Sci. (2002) [Pubmed]
  18. Use of carbohydrases in corn-soybean meal-based nursery diets. Kim, S.W., Knabe, D.A., Hong, K.J., Easter, R.A. J. Anim. Sci. (2003) [Pubmed]
  19. Evidence for an adenosine receptor on the surface of dog coronary myocytes. Olsson, R.A., Davis, C.J., Khouri, E.M., Patterson, R.E. Circ. Res. (1976) [Pubmed]
  20. Membrane lipid dynamics in human promyelocytic leukemia cells sensitive and resistant to 12-O-tetradecanoylphorbol-13-acetate induction of differentiation. Fisher, P.B., Schachter, D., Abbott, R.E., Callaham, M.F., Huberman, E. Cancer Res. (1984) [Pubmed]
  21. Fagopyritol B1, O-alpha-D-galactopyranosyl-(1-->2)-D-chiro-inositol, a galactosyl cyclitol in maturing buckwheat seeds associated with desiccation tolerance. Horbowicz, M., Brenac, P., Obendorf, R.L. Planta (1998) [Pubmed]
  22. Some carbohydrates found in pollen and pollen substitutes are toxic to honey bees. Barker, R.J. J. Nutr. (1977) [Pubmed]
  23. Effect of dietary supplementation with alpha-galactosidase preparation and stachyose on growth performance, nutrient digestibility and intestinal bacterial populations of piglets. Pan, B., Li, D., Piao, X., Zhang, L., Guo, L. Archiv für Tierernährung. (2002) [Pubmed]
  24. A poly(ethylene glycol) water-soluble conjugate of porin: refolding to the native state. Wei, J., Fasman, G.D. Biochemistry (1995) [Pubmed]
  25. Purification and characterization of stachyose synthase from lentil (Lens culinaris) seeds: galactopinitol and stachyose synthesis. Hoch, G., Peterbauer, T., Richter, A. Arch. Biochem. Biophys. (1999) [Pubmed]
  26. Anti-nutritional constituents of six underutilized legumes grown in Nigeria. Oboh, H.A., Muzquiz, M., Burbano, C., Cuadrado, C., Pedrosa, M.M., Ayet, G., Osagie, A.U. Journal of chromatography. A. (1998) [Pubmed]
  27. Lectin like properties and differential sugar binding characteristics of C-reactive proteins purified from sera of normal and pollutant induced Labeo rohita. Mandal, C., Sinha, S., Mandal, C. Glycoconj. J. (1999) [Pubmed]
  28. Isolation and characterization of a low molecular weight complement inhibitor present in normal human serum. Baker, P.J., Osofsky, S.G. Clin. Exp. Immunol. (1981) [Pubmed]
  29. Isolation of an antigenic oligosaccharide fraction from Leptospira interrogans serovar canicola with a monoclonal antibody. Ono, E., Naiki, M., Yanagawa, R. J. Gen. Microbiol. (1984) [Pubmed]
  30. Reaction mechanism and fragment ion structure determination of deprotonated small oligosaccharides, studied by negative ion fast atom bombardment (tandem) mass spectrometry. Dallinga, J.W., Heerma, W. Biol. Mass Spectrom. (1991) [Pubmed]
  31. Development and composition of the seeds of nine genotypes of the Medicago truncatula species complex. Djemel, N., Guedon, D., Lechevalier, A., Salon, C., Miquel, M., Prosperi, J.M., Rochat, C., Boutin, J.P. Plant Physiol. Biochem. (2005) [Pubmed]
 
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